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Fully conjugated [4] chrysaorene. Redox-coupled anion binding in a tetraradicaloid macrocycle

Gregolinska, Hanna, Majewski, Marcin, Chmielewski, Piotr J., Gregolinski, Janusz, Chien, Alan, Zhou, Jiawang, Wu, Yi-Lin, Bae, Youn Jue, Wasielewski, Michael R., Zimmerman, Paul M. and Stepien, Marcin 2018. Fully conjugated [4] chrysaorene. Redox-coupled anion binding in a tetraradicaloid macrocycle. Journal of the American Chemical Society 140 (43) , pp. 14474-14480. 10.1021/jacs.8b09385

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Abstract

[4]Chrysaorene, a fully conjugated carbocyclic coronoid, is shown to be a low-bandgap π-conjugated system with a distinct open-shell character. The system shows good chemical stability and can be oxidized to well-defined radical cation and dication states. The cavity of [4]chrysaorene acts as an anion receptor toward halide ions with a particular selectivity toward iodides (Ka = 207 ± 6 M–1). The interplay between anion binding and redox chemistry is demonstrated using a 1H NMR analysis in solution. In particular, a well-resolved, paramagnetically shifted spectrum of the [4]chrysaorene radical cation is observed, providing evidence for the inner binding of the iodide. The radical cation–iodide adduct can be generated in thin solid films of [4] chrysaorene by simple exposure to diiodine vapor.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Date of First Compliant Deposit: 31 July 2019
Date of Acceptance: 5 October 2018
Last Modified: 27 May 2020 13:30
URI: http://orca.cf.ac.uk/id/eprint/124621

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